San Gimignano is one of Tuscany’s prettiest and most famous small medieval hilltop towns. With a name that translates as the ‘Town of Fine Towers,’ it’s best known for its well-preserved medieval towers and encircling walls, which give it an unmistakable skyline. Inside the walls, its impressive buildings include notable examples of Romanesque and Gothic architecture.

Travel through the Chianti region. This area of Tuscany boasts of endless rolling hills covered with grain or sunflowers, a rich green valley with vineyards. It is no wonder that this territory is protected as a World Heritage Site by UNESCO like Castellina. The quaint Etruscan village is home to a fortress that dates back to the 15th century. Wine Tasting included.

Monteriggioni is a medieval walled town, located on a natural hillock, built in 1214–19. During the conflicts between Siena and Florence in the Middle Ages, the city was strategically placed as a defensive fortification. It also withstood many attacks from both the Florentines and the forces of the Bishop of Volterra.